Pyridine → (S)-[2-(Hydroxylimino)-2-(4-methoxyphenyl)-1-phenylethyl]carbamic Acid Benzyl Ester

Participants

Reaction Conditions

Reaction Steps

To a solution of the ketone 483 (2.47 g, 6.6 mmol) in EtOH (35 mL) is added hydroxylamine hydrochloride (1.83 g, 26.4 mmol) followed by pyridine (2.13 mL, 26.4 mmol). The mixture is stirred at 80° C. for 8 h. The reaction mixture is cooled, the solvent is evaporated, and the residue dissolved in EtOAc, washed with water, brine, then dried (MgSO4), and filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with heptane:EtOAc (7:3) gives 1.95 g of the product 484. 1H NMR (CDCl3) δ 7.55 (d, 2H), 7.50-7.10 (m, 10H), 7.00-6.70 (m, 2H), 6.50-6.35 (m, 1H), 5.30-5.00 (m, 2H), 3.80 (d, 3H); MS: m/z 391 (M++1).

Provenance & Evidence